diff --git a/app/Console/Commands/CheckData.php b/app/Console/Commands/CheckData.php
index fd3f8543df..4935371bed 100644
--- a/app/Console/Commands/CheckData.php
+++ b/app/Console/Commands/CheckData.php
@@ -64,7 +64,7 @@ class CheckData extends Command
 
     public function fire()
     {
-        $this->logMessage(date('Y-m-d') . ' Running CheckData...');
+        $this->logMessage(date('Y-m-d h:i:s') . ' Running CheckData...');
 
         if ($database = $this->option('database')) {
             config(['database.default' => $database]);
diff --git a/app/Console/Commands/UpdateKey.php b/app/Console/Commands/UpdateKey.php
new file mode 100644
index 0000000000..d2c1b2f209
--- /dev/null
+++ b/app/Console/Commands/UpdateKey.php
@@ -0,0 +1,80 @@
+<?php
+
+namespace App\Console\Commands;
+
+use Illuminate\Console\Command;
+use Symfony\Component\Console\Input\InputOption;
+use App\Models\AccountGateway;
+use App\Models\BankAccount;
+use Artisan;
+use Crypt;
+use Illuminate\Encryption\Encrypter;
+
+/**
+ * Class PruneData.
+ */
+class UpdateKey extends Command
+{
+    /**
+     * @var string
+     */
+    protected $name = 'ninja:update-key';
+
+    /**
+     * @var string
+     */
+    protected $description = 'Update application key';
+
+    public function fire()
+    {
+        $this->info(date('Y-m-d h:i:s') . ' Running UpdateKey...');
+
+        // load the current values
+        $gatewayConfigs = [];
+        $bankUsernames = [];
+
+        foreach (AccountGateway::all() as $gateway) {
+            $gatewayConfigs[$gateway->id] = $gateway->getConfig();
+        }
+
+        foreach (BankAccount::all() as $bank) {
+            $bankUsernames[$bank->id] = $bank->getUsername();
+        }
+
+        // set the new key and create a new encrypter
+        Artisan::call('key:generate');
+        $key = base64_decode(str_replace('base64:', '', config('app.key')));
+        $crypt = new Encrypter($key, config('app.cipher'));
+
+        // update values using the new key/encrypter
+        foreach (AccountGateway::all() as $gateway) {
+            $config = $gatewayConfigs[$gateway->id];
+            $gateway->config = $crypt->encrypt(json_encode($config));
+            $gateway->save();
+        }
+
+        foreach (BankAccount::all() as $bank) {
+            $username = $bankUsernames[$bank->id];
+            $bank->username = $crypt->encrypt($username);
+            $bank->save();
+        }
+
+        $this->info(date('Y-m-d h:i:s') . ' Successfully updated the application key');
+    }
+
+    /**
+     * @return array
+     */
+    protected function getArguments()
+    {
+        return [];
+    }
+
+    /**
+     * @return array
+     */
+    protected function getOptions()
+    {
+        return [];
+    }
+}
diff --git a/app/Console/Kernel.php b/app/Console/Kernel.php
index 46ab045be1..f43e8fafaa 100644
--- a/app/Console/Kernel.php
+++ b/app/Console/Kernel.php
@@ -29,6 +29,7 @@ class Kernel extends ConsoleKernel
         'App\Console\Commands\MakeClass',
         'App\Console\Commands\InitLookup',
         'App\Console\Commands\CalculatePayouts',
+        'App\Console\Commands\UpdateKey',
     ];
 
     /**
diff --git a/app/Listeners/HandleUserLoggedIn.php b/app/Listeners/HandleUserLoggedIn.php
index d25fe5fcaf..2e0e058e51 100644
--- a/app/Listeners/HandleUserLoggedIn.php
+++ b/app/Listeners/HandleUserLoggedIn.php
@@ -71,19 +71,24 @@ class HandleUserLoggedIn
             Session::flash('warning', trans('texts.logo_too_large', ['size' => $account->getLogoSize() . 'KB']));
         }
 
-        // check custom gateway id is correct
         if (! Utils::isNinja()) {
+            // check custom gateway id is correct
             $gateway = Gateway::find(GATEWAY_CUSTOM);
             if (! $gateway || $gateway->name !== 'Custom') {
                 Session::flash('error', trans('texts.error_incorrect_gateway_ids'));
             }
-            /*
+
+            // if APP_KEY isn't set use the default
             if (! env('APP_KEY')) {
-                Session::flash('error', trans('texts.error_app_key_not_set'));
-            } elseif (in_array(, ['SomeRandomString', 'SomeRandomStringSomeRandomString', 'AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA'])) {
+                $fp = fopen(base_path().'/.env', 'a');
+                fwrite($fp, "\nAPP_KEY=" . config('app.key'));
+                fclose($fp);
+            }
+
+            // warn if using the default app key
+            if (in_array(config('app.key'), ['SomeRandomString', 'SomeRandomStringSomeRandomString', 'AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA'])) {
                 Session::flash('error', trans('texts.error_app_key_set_to_default'));
             }
-            */
         }
     }
 }
diff --git a/app/Models/BankAccount.php b/app/Models/BankAccount.php
index 2cd4a65646..a5365ee9f8 100644
--- a/app/Models/BankAccount.php
+++ b/app/Models/BankAccount.php
@@ -2,6 +2,7 @@
 
 namespace App\Models;
 
+use Crypt;
 use Illuminate\Database\Eloquent\SoftDeletes;
 
 /**
@@ -33,6 +34,22 @@ class BankAccount extends EntityModel
         return ENTITY_BANK_ACCOUNT;
     }
 
+    /**
+     * @return mixed
+     */
+    public function getUsername()
+    {
+        return Crypt::decrypt($this->username);
+    }
+
+    /**
+     * @param $config
+     */
+    public function setUsername($value)
+    {
+        $this->username = Crypt::encrypt($value);
+    }
+
     /**
      * @return \Illuminate\Database\Eloquent\Relations\BelongsTo
      */
diff --git a/resources/lang/en/texts.php b/resources/lang/en/texts.php
index d10b981163..f1042d9844 100644
--- a/resources/lang/en/texts.php
+++ b/resources/lang/en/texts.php
@@ -2302,8 +2302,7 @@ $LANG = array(
     'app_version' => 'App Version',
     'ofx_version' => 'OFX Version',
     'gateway_help_23' => ':link to get your Stripe API keys.',
-    'error_app_key_not_set' => 'Error: the APP_KEY value is not set in the .env file.',
-    'error_app_key_set_to_default' => 'Error: the APP_KEY value is set to the default in the .env file.',
+    'error_app_key_set_to_default' => 'Error: APP_KEY is set to a default value, to update it backup your database and then run <code>php artisan ninja:update-key</code>',
     'charge_late_fee' => 'Charge Late Fee',
     'late_fee_amount' => 'Late Fee Amount',
     'late_fee_percent' => 'Late Fee Percent',